Personal & Executive Assistant / Lifestyle Coordinator — Chicago

Personal & Executive Assistant / Lifestyle Coordinator — Chicago

We are looking for an exceptional, highly organized and proactive personal assistant to support two busy professionals in Chicago.

This is not a housekeeping role. We are looking for someone who can become the organizational center of our lives — helping us manage schedules, travel, social commitments, personal projects and several new business ventures while making everything run more smoothly and efficiently.

The ideal person is someone who genuinely loves organization, thinks ahead, solves problems quickly and enjoys creating systems that make busy lives easier.

Responsibilities may include:

• Managing calendars, appointments and daily schedules
• Coordinating flights, hotels, transportation and travel itineraries
• Organizing social plans, dinners, events and reservations
• Helping coordinate new business projects and keeping projects moving
• Researching vendors, services, purchases and opportunities
• Managing personal appointments and reminders
• Helping organize our weeks so our time is used more effectively
• Creating and maintaining to-do lists, project trackers and follow-up systems
• Coordinating our cleaning lady and other service providers
• Managing deliveries, packages, returns and occasional errands
• Coordinating plant care and other basic household needs
• Assisting with social media planning, content coordination and scheduling where appropriate
• Helping prepare for travel before we leave and keeping things organized while we are away
• Making sure important tasks do not fall through the cracks
• Generally looking for ways to make our personal and professional lives easier and more efficient

There will be a mixture of personal, social and business responsibilities, so discretion and good judgment are extremely important.

We are looking for someone who can eventually understand our routines and anticipate what needs to happen without needing constant direction.

You might be a great fit if you are:

• Extremely organized
• Proactive and resourceful
• Warm, personable and easy to work with
• Naturally good at planning and logistics
• Excellent at communicating by text, email and phone
• Comfortable managing multiple priorities at once
• Tech-savvy and comfortable with calendars, travel apps, spreadsheets and organizational tools
• Good at researching and presenting options
• Comfortable communicating with vendors and service providers
• Discreet and trustworthy
• Flexible when plans change
• Someone who enjoys figuring things out rather than waiting to be told every next step

Previous experience as a personal assistant, executive assistant, lifestyle assistant, project coordinator, hospitality professional or similar role is preferred.

Experience with social media, event planning, travel coordination or startup/new-business environments would be a strong plus.

Location: Chicago
Schedule: Approximately 15–20 hours per week
Compensation: $25/hour

Some work can be handled remotely, but we want someone based in Chicago who can also be physically present when needed.

This role has the potential to become an important long-term position for the right person. We are looking for someone who wants to truly learn our lives, help us build better systems and become a trusted right hand to both of us.

To apply:

Please send your resume along with a short introduction telling us:

• Why this type of role appeals to you
• The most complicated personal or professional schedule you have managed
• An example of something you organized or improved without being asked
• Your availability

Professional references and a background check will be required.

Pay: $25.00 per hour

Expected hours: 15.0 – 20.0 per week

Benefits:

• Flexible schedule
• Professional development assistance

Work Location: Hybrid remote in Chicago, IL 60640